The invention relates to novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings, a plurality of processes for their preparation and their use as herbicides and insecticides.
It is already known that certain N-cyanoaryl nitrogen heterocycles have herbicidal properties (cf. WO-A 91/00278, WO-A 92/11244, EP-A 408382, EP-A 438209, EP-A 473551, DE-A 4237920). However, the herbicidal action and the compatibility of the previously known N-cyanoaryl nitrogen heterocycles with cultivated plants are not entirely satisfactory.
The novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings of the general formula (I) have now been found, 
in which
Q1 represents oxygen or sulphur,
R1 represents hydrogen or halogen,
R2 represents halogen, cyano, nitro, amino or the grouping xe2x80x94N(A1)SO2A, in which
A represents, in each case, optionally substituted alkyl, alkenyl, alkinyl, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, and
A1 represents hydrogen, formyl or, in each case optionally substituted, alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl, or
together with A represents alkanediyl,
R3 represents hydrogen, halogen, cyano or optionally substituted alkyl,
R4 represents optionally substituted alkyl or together with R3 represents alkanediyl, and
Z represents one of the groupings below 
xe2x80x83in which
Q2 represents oxygen or sulphur and
R5 represents hydrogen or, in each case optionally substituted, alkyl, alkenyl, alkinyl or alkylcarbonyl,
and salts of compounds of the formula (I)
with the proviso that at least one of the groupings Q1 or Q2 represents sulphur.
The general formula (I) therefore represents the isomeric compounds of the general formulae (IA) and (IB) below 
The novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings of the general formula (I) are obtained if
(a) aminoalkenoic (thio)esters of the general formula (II) 
xe2x80x83in which
Q1, R3, R4 and R5 have the meanings given above and
R represents alkyl,
are reacted with cyanoaryl iso(thio)cyanates of the general formula (III) 
xe2x80x83in which
Q2, R1 and R2 have the meanings given above,
in the presence or absence of a reaction auxiliary and in the presence or absence of a diluent,
or if
(b) for the preparation of compounds of the formulae (IA) and/or (IB) in which R5 represents, in each case optionally substituted, alky, alkenyl or alkinyl and Q1, Q2, R1, R2, R3 and R4 have the meanings given above,
N-cyanoaryl nitrogen heterocycles of the general formula (IA) or (IB)
in which R5 represents hydrogen and Q1, Q2, R1, R2, R3 and R4 have the meanings given above,
are reacted with alkylating agents of the general formula (IV) or (V)
Xxe2x80x94R5xe2x80x83xe2x80x83(IV)
R5xe2x80x94Oxe2x80x94SO2xe2x80x94Oxe2x80x94R5xe2x80x83xe2x80x83(V)
in which R5 represents, in each case optionally substituted, alkyl, alkenyl or alkinyl,
in the presence or absence of an acid acceptor and in the presence or absence of a diluent,
or if
(c) for the preparation of compounds of the formula (I) in which R2 represents amino or the grouping xe2x80x94N(A1)SO2A and A, A1, Q1, Q2, R1, R3, R4 and Z have the meanings given above,
N-cyanoaryl nitrogen heterocycles of the general formula (I), in which R2 represents halogen and Q1, Q2, R1, R3, R4 and Z have the meanings given above,
are reacted with ammonia or with amides of the general formula (VI)
HN(A1)SO2Axe2x80x83xe2x80x83(VI)
in which
A and A1 have the meanings given above,
in the presence or absence of an acid acceptor and in the presence or absence of a diluent.
The compounds of the formula (I) can, by analogy with process (a), also be obtained by reaction of aminoalkenoic (thio)esters of the formula (II)xe2x80x94abovexe2x80x94with cyanoaryl (thio)urethanes of the formula (IIIa) 
in which
Q2, R1 and R2 have the meanings given above and
R represents alkyl (in particular methyl) or aryl (in particular phenyl).
The novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings of the general formula (I) are distinguished by high herbicidal efficiency.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are each straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably relates to compounds of the formula (I) in which
Q1 represents oxygen or sulphur,
R1 represents hydrogen, fluorine, chlorine or bromine,
R2 represents fluorine, chlorine, bromine, cyano, nitro, amino or the grouping xe2x80x94N(A1)SO2A, in which
A represents a radical selected from the group consisting of alkyl, alkenyl, alkinyl or dialkylamino each having up to 10 carbon atoms and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy,
A further represents cycloalkyl or cycloalkylalkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkyl, having 3 to 8 carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
A further represents aryl or arylalkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, by C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which are each optionally substituted by fluorine and/or chlorine), by dimethylaminosulphonyl or diethylaminosulphonyl, by C1-C4-alkoxy-carbonyl (which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy), by phenyl or phenyloxy (which are each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy), having 6 or 10 carbon atoms in the aryl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, and
A1 represents hydrogen or formyl, or C1-C4-alkyl which is optionally substituted by fluorine and/or chlorine, cyano or C1-C4-alkoxy-carbonyl, or C1-C4-alkyl-carbonyl or C1-C4-alkoxy-carbonyl, each of which is optionally substituted by fluorine, chlorine or C1-C4-alkoxy, or C1-C4-alkylsulphonyl which is optionally substituted by fluorine and/or chlorine, or
together with A represents alkanediyl having 2 to 8 carbon atoms,
R3 represents hydrogen, fluorine, chlorine, bromine, cyano or alkyl, which is optionally substituted by fluorine and/or chlorine, having 1 to 4 carbon atoms,
R4 represents alkyl, which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy, having 1 to 6 carbon atoms,
or together with R3 represents alkanediyl having 2 to 8 carbon atoms, and
Z represents one of the groupings below 
xe2x80x83in which
Q2 represents oxygen or sulphur and
R5 represents hydrogen or alkyl, alkenyl, alkinyl or alkylcarbonyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C1-C4-alkyl-carbonyl or C1-C4-alkoxy-carbonyl, and each of which has up to 6 carbon atoms,
with the proviso that at least one of the groupings Q1 or Q2 represents sulphur.
The invention further preferably relates to sodium salts, potassium salts, calcium salts, ammonium salts, C1-C4-alkyl-ammonium salts, di-(C1-C4-alkyl)-ammonium salts, tri-(C1-C4-alkyl)-ammonium salts, cyclopentyl- or cyclohexyl-ammonium salts and di-(C1-C4-alkyl)-ammonium salts of compounds of the formula (I) in which Q1, R1, R2, R3, R4 and Z have the meaning given above as preferred.
The invention relates in particular to compounds of the formula (I) in which
Q1 represents oxygen or sulphur,
R1 represents hydrogen, fluorine or chlorine,
R2 represents fluorine, chlorine, bromine, cyano, amino or the grouping xe2x80x94N(A1)SO2A, in which
A represents a radical selected from the group consisting of methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethenyl, propenyl, butenyl, each of which is optionally substituted by fluorine or chlorine, or represents dimethylamino,
A further represents cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl and/or ethyl,
A further represents phenyl, naphthyl, phenylmethyl or phenylethyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxy, methyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, dimethylaminosulphonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl or phenyl, and
A1 represents hydrogen, formyl, methyl, ethyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or ethylsulphonyl, or together with A represents trimethylene or tetramethylene,
R3 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, n- or i-propyl,
R4 represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by fluorine or chlorine, or together with R3 represents trimethylene or tetramethylene, and
Z represents one of the groupings below 
xe2x80x83in which
Q2 represents oxygen or sulphur and
R5 represents hydrogen, methyl, difluoromethyl, cyanomethyl, ethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, trifluoroethyl, chlorodifluoroethyl, cyanoethyl, n- or i-propyl, fluoropropyl, chloropropyl, cyanopropyl, allyl, chloroallyl, propargyl, acetyl, propionyl, fluoroacetyl, chloroacetyl, difluoroacetyl, dichloroacetyl, trifluoroacetyl or trichloroacetyl,
with the proviso that at least one of the groupings Q1 or Q2 represents sulphur.
A very particularly preferred group of compounds of the formula (I) are the compounds of the formula (IA) in which Q1 represents oxygen, Q2 represents sulphur, and R1, R2, R3, R4 and R5 have the meaning given above as preferred in particular.
A further very particularly preferred group of compounds of the formula (I) are the compounds of the formula (IB) in which Q1 represents oxygen, Q2 represents sulphur, and R1, R2, R3, R4 and R4 have the meaning given above as preferred in particular.
The general radical definitions or the radical definitions given in preferred areas listed above apply not only to the end products of the formula (I) but also correspondingly to each of the starting materials or intermediates necessary for preparation. These radical definitions can be combined in any manner with one another, that is also between the given ranges of preferred compounds.
Examples of the compounds of the invention of the formula (IA)xe2x80x94where in each case Q1 represents oxygen and Q2 represents sulphurxe2x80x94are listed in Table 1 below.
If, for example, methyl 3-aminocrotonate and 4-cyano-2,5-difluoro-phenyl isothio-cyanate are used as starting materials, the course of the reaction in the process (a) of the invention can be outlined by the following formula scheme: 
If, for example, 1-(3-chloro-4-cyano-phenyl)-3,6-dihydro-6-oxo-2-thioxo-4-trifluoro-methyl-1(2H)-pyrimidine and methyl bromide are used as starting materials, the course of the reaction in the process (b) of the invention can be outlined by the following formula scheme: 
If, for example, 1-(4-cyano-2,5-difluoro-phenyl)-3,6-dihydro-3,4-dimethyl-2-oxo-6-thioxo-1(2H)-pyrimidine and ethanesulphonamide are used as starting materials, the course of the reaction in the process (c) of the invention can be outlined by the following formula scheme: 
The aminoalkenoic (thio)esters to be used as starting materials for the preparation of compounds of the formula (I) in the process (a) of the invention are generally defined by the formula (II).
In formula (II), Q1, R3 and R4 preferably or in particular have that meaning which has already been given above in connection with the description of the compounds of the invention of the formula (I) as preferred or preferred in particular for Q1, R3 and R4;
R preferably represents C1-C4-alkyl, in particular methyl or ethyl.
The starting materials of the formula (II) are known and/or can be prepared by known processes (cf J. Heterocycl. Chem. 9 (1972), 513-522).
The cyanoaryl iso(thio)cyanates further to be used as starting materials in the process (a) of the invention are generally defined by the formula (III).
In formula (III), Q2, R1 and R2 preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the invention of the formula (I) as preferred or preferred in particular for Q2, R1 and R2.
The starting materials of the formula (III) are known and/or can be prepared by known processes (cf. J. Org. Chem. 30 (1965), 2465-2466; cf. also DE-P 4327743 and DE-P 4335438).
The cyanoaryl iso(thio)cyanates of the formula (III) are obtained if corresponding cyanoarylamines of the general formula (VII) 
in which
R1 and R2 have the meaning given above,
are reacted with phosgene or thiophosgene, in the presence or absence of a reaction auxiliary, such as calcium carbonate, and in the presence or absence of diluents, such as methylene chloride, toluene, chlorobenzene and, if appropriate, water, at temperatures between 0xc2x0 C. and 150xc2x0 C. (cf. the preparation examples).
The process (a) of the invention for the preparation of the novel compounds of the formula (I) is preferably carried out using diluents. The diluents which are suitable here are virtually all inert organic solvents. These preferably include aliphatic and aromatic, nonhalogenated or halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichloro-benzene, ethers, such as diethyl ether and dibutyl ether, glycol dimethyl ether and di-glycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone and dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.
The process (a) of the invention is preferably carried out in the presence of a reaction auxiliary. Reaction auxiliaries which are suitable here are principally acid acceptors. Preferably, those which are used are alkali metal hydrides and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal carbonates and hydrogen carbonates and alkaline earth metal carbonates and hydrogen carbonates, such as sodium carbonate or hydrogen carbonate and potassium carbonate or hydrogen carbonate and calcium carbonate, alkali metal acetates, such as sodium acetate and potassium acetate, alkali metal alkoxides, such as sodium methoxide, ethoxide, propoxide, isopropoxide, butoxide, isobutoxide and tert-butoxide and potassium methoxide, ethoxide, propoxide, isopropoxide, butoxide, isobutoxide and tert-butoxide, in addition basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2,2,2]-octane (DABCO).
The reaction temperatures can be varied in a relatively wide range in the process (a) of the invention. Generally, temperatures between xe2x88x92120xc2x0 C. and +100xc2x0 C. are employed, preferably temperatures between xe2x88x9270xc2x0 C. and +80xc2x0 C.
The process (a) of the invention is generally carried out at atmospheric pressure. However, it is also possible to employ elevated or reduced pressure.
To carry out the process (a) of the invention, the starting materials needed in each case are generally used in approximately equimolar amounts. However, it is also possible to employ one of the two components used in each case in a relatively great excess. The reactions are generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is stirred for a plurality of hours at the temperature required in each case. The workup in the process (a) of the invention is performed in each case by conventional methods (cf. the preparation examples).
The N-cyanoaryl nitrogen heterocycles to be used as starting materials for the preparation of compounds of the formula (I) in the process (b) of the invention are generally defined by the formulae (IA) and (IB)xe2x80x94with the proviso that R5 represents hydrogen therein.
In the formulae (IA) and (IB), Q1, Q2, R1, R2, R3 and R4 preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the invention of the formula (I) as preferred or preferred in particular for Q1, Q2, R1, R2, R3 and R4.
The starting materials of the formulae (IA) and (B) for process (b) are novel compounds of the invention, they can be prepared by the process (a) of the invention.
The alkylating agents further to be used as starting materials in the process (b) of the invention are generally defined by the formulae (IV) and (V).
In the formulae (IV) and (V), R5 preferably or in particular has that meaning which has already been given above in connection with the description of the compounds of the invention of the formula (I) as preferred or preferred in particular for R5.
The starting materials of the formulae (IV) and (V) are known organic synthesis chemicals.
The process (b) of the invention is preferably carried out using a diluent. Those diluents are suitable here, principally, which have already been mentioned in the description of the process (a) of the invention.
Acid acceptors which can be used in the process (b) of the invention are all acid binders which are conventionally usable for such reactions. Preferably, those which can be used are alkali metal hydrides and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal carbonates and hydrogen carbonates and alkaline earth metal carbonates and hydrogen carbonates, such as sodium carbonate or hydrogen carbonate and potassium carbonate or hydrogen carbonate and calcium carbonate, alkali metal acetates, such as sodium acetate and potassium acetate, alkali metal alkoxides, such as sodium methoxide, ethoxide, propoxide, isopropoxide, butoxide, isobutoxide and tert-butoxide and potassium methoxide, ethoxide, propoxide, isopropoxide, butoxide, isobutoxide and tert-butoxide, in addition basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2,2,2]-octane (DABCO).
The reaction temperatures in the process (b) of the invention can be varied within a relatively wide range. Generally, temperatures between 0xc2x0 C. and 120xc2x0 C. are employed, preferably temperatures between 10xc2x0 C. and 100xc2x0 C.
The process (b) of the invention is generally carried out at atmospheric pressure. However, it is also possible to employ elevated or reduced pressure.
To carry out the process (b) of the invention, the starting materials needed in each case are generally used in approximately equimolar amounts. However, it is also possible to employ one of the two components used in each case in a relatively great excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a plurality of hours at the temperature required in each case. The workup in the process (b) of the invention is carried out in each case by conventional methods (cf. the preparation examples).
The N-cyanoaryl nitrogen heterocycles to be used as starting materials for the preparation of compounds of the formula (I) in the process (c) of the invention are generally defined by the formula (I)xe2x80x94with the proviso that R2 represents halogen therein.
In formula (I), Q1, Q2, R1, R3, R4 and Z preferably or in particular then have those meanings which have already been given above as preferred or as preferred in particular for Q1, Q2, R1, R3, R4 and Z in connection with the description of the compounds of the formula (I) of the invention.
The starting materials of the formula (I) for process (c) are novel compounds of the invention; they can be prepared by the processes (a) and (b) of the invention.
The amides further to be used as starting materials in the process (c) of the invention are generally defined by the formula (VI).
In formula (VI), A and A1 preferably or in particular have that meaning which has already been given above as preferred or preferred in particular for A and A1 in connection with the description of the compounds of the formula (I) of the invention.
The starting materials of the formula (VI) are known organic synthesis chemicals.
The process (c) of the invention is preferably carried out using a diluent. Those diluents which are suitable here are principally those which have already been mentioned in the description of the process (a) of the invention.
The process (c) of the invention is carried out in the presence or absence of an acid acceptor. Those acid acceptors are suitable here which have already been mentioned in the description of the process (b) of the invention.
The reaction temperatures in the process (c) of the invention can be varied in a relatively broad range. Generally, temperatures between 0xc2x0 C. and 200xc2x0 C. are employed, preferably temperatures between 20xc2x0 C. and 180xc2x0 C.
The process (c) of the invention is generally carried out at atmospheric pressure. However, it is also possible to employ elevated or reduced pressure.
To carry out the process (c) of the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to employ one of two components used in each case in a relatively great excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a plurality of hours at the temperature required in each case. The workup in the process (c) of the invention is performed in each case by conventional methods (cf. the preparation examples).
The active compounds of the invention can be used as defoliants, desiccants, herbicides and, in particular, as weed killers. Weeds in the broadest sense are taken to mean all plants which grow at places where they are not desired. Whether the substances of the invention act as total or selective herbicides essentially depends on the application rate.
The active compounds of the invention can be used, eg., in the case of the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Panunculus and Taraxacum.
Dicotyledonous cultivated plants of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoca, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledonous cultivated plants of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds of the invention is in no way restricted to these genera, but also extends in a similar manner to other plants.
The compounds, depending on the concentration, are suitable for total weed control, eg. on industrial areas and railway tracks and on paths and grounds with or without tree growth. Likewise, the compounds can be used for weed control in permanent cultivation, eg. forest, ornamental wood plantations, fruit cultivation, vineyards, citrus plantations, nut plantations, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, berry fruit plantations and hopfields, on ornamental lawns and sports fields and grazing areas and for selective weed control in annual cultivations.
The compounds of the formula (I) of the invention are suitable, in particular, for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous cultivations both in the preemergence and postemergence methods.
The active compounds are also suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forestry, in the protection of stored products and materials and in the hygiene sector. They are active against species of usual sensitivity and resistance and against all or individual development stages. The pests mentioned above include:
From the order of the Isopoda, eg. Oniscus asellus, Armadillidium vulgare and Porcellio scaber. 
From the order of the Diplopoda, eg. Blaniulus guttulatus. 
From the order of the Chilopoda, eg. Geophilus carpophagus and Scutigera spec.
From the order of the Symphyla, eg. Scutigerella immaculata. 
From the order of the Thysanura, eg. Lepisma saccharina. 
From the order of the Collembola, eg. Onychiurus armatus. 
From the order of the Orthoptera, eg. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. 
From the order of the Dermaptera, eg. Forficula auricularia. 
From the order of the Isoptera, eg. Reticulitermes spp.
From the order of the Anoplura, eg. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, eg. Trichodectes spp. and Damalinea spp.
From the order of the Thysanoptera, eg. Hercinothrips femoralis and Thrips tabaci. 
From the order of the Heteroptera, eg. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, eg. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, eg. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Caprocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana. 
From the order of the Coleoptera, eg. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica. 
From the order of the Hymenoptera, eg. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, eg. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. 
From the order of the Siphonaptera, eg. Xenopsylla cheopis and Ceratophyllus spp.
From the order of the Arachnida, eg. Scorpio maurus and Latrodectus mactans. 
From the order of the Acarina, eg. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.
The phytopathogenic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp.
The active compounds can be converted into the conventional formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension/emulsion concentrates, natural and synthetic materials impregnated with active compound and very fine encapsulations in polymeric materials.
These formulations are prepared in a known manner, eg. by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, with or without the use of surfactants, that is emulsifiers and/or dispersants and/or foam-forming agents.
In the case of the use of water as extender, eg. organic solvents can also be used as solubilizer. Liquid solvents which are suitable are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, eg. mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, highly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
Solid carriers which are useful are:
eg. ammonium salts and natural rock flours, such as kaolins, clays, talcum, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminium oxide and silicates; solid carriers for granules which are suitable are: eg. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; emulsifiers and/or foam-forming agents which are suitable are: eg. nonionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxythylene fatty alcohol ethers, eg. alkylaryl polyglycol ethers, alkylsulphonates, alkyl-sulphates, arylsulphonates and protein hydrolysates; dispersants which are suitable are: eg. lignin sulphite liquors and methylcellulose.
In the formulations, binding agents such as carboxymethylcellulose, natural and synthetic pulverulent, granular or latex-like polymers, can be used, such as gum arabic, poly(vinyl alcohol), poly(vinyl acetate), and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.
Colourants can be used, such as inorganic pigments, eg. iron oxide, titanium oxide, Prussian Blue and organic colourants, such as alizarin, azo and metallophthalocyanine colourants and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
The active compounds of the invention can also be used as such or in their formulations in a mixture with known herbicides for weed control, ready-to-use formulations or tank mixtures being possible.
Known herbicides are suitable for the mixtures, for example anilides such as diflufenican and propanil; arylcarboxylic acids such as dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as 2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters such as diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones such as chloridazon and norflurazon; carbamates such as chlorpropham, desmedipham, phen-medipham and propham; chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines such as oryzalin, pendimethalin and trifluralin; diphenyl ethers such as acifluorfen, bifenox, fluoro-glycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as bromoxynil, dichlobenil and ioxynil; oxyacetamides such as mefenacet; sulphonylureas such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, met-sulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiolcarbamates such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines such as atrazine, cyanazine, simazine, simetryne, terbutryne and terbuthylazine; triazinones such as hexazinone, metamitron and metribuzin; others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinclorac, quinmerac, sulphosate and tridiphane.
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers is also possible.
The active compounds can be applied as such, in the form of their formulations or the application forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are applied in a conventional manner, eg. by pouring, sprinkling, spraying, scattering.
The active compounds of the invention can be applied either before or after the emergence of plants. They can also be incorporated into the soil before sowing.
The active compound application rate can vary in a relatively broad range. It essentially depends on the type of effect desired. Generally, the application rates are between 10 g and 10 kg of active compound per hectare of soil surface, preferably between 50 g and 5 kg per ha.